On the night of the fight Tyson was astronomically favored over Douglas, a 42-1 underdog. This translates as someone who bet $100 on Douglas would receive $4200 in return.

Odds of 10-1 are considered to be one-sided, but 42-1 is flat-out unheard of.

Tyson was the biggest thing in boxing at that time; he was the undisputed heavyweight champion of the world.

Going into the fight Tyson had a record of 37-0 with 33 knockouts, 17 of those occurring in round one. Many felt that Tyson was in the process of becoming perhaps the greatest heavyweight of all time.

Douglas, on the other hand, was considered a mere journeyman fighter—a fighter with average skills that was never expected to excel in the sport.

Douglas had a previous title shot, three years prior to the Tyson fight, for the vacant IBF (International Boxing Federation) heavyweight title which he lost by a tenth round technical-knockout to Tony Tucker. Coming into the Tyson fight, Douglas had a record of 29-4-1 no contest.

While Douglas’ career up to that point was met with mixed success it was not the only reason he was seen as such a large underdog.

Douglas’ mother, whom he was incredibly close with, died less than a month before the fight.

As if dealing with the emotional stress of his mother’s death wasn’t enough, Douglas also contracted the flu the day before the fight.

Needless to say, many were skeptical that Douglas would be in the right frame of mind for such a big fight.

The general consensus was that the fight with Douglas was simply a tune-up for Tyson who was expected to have a highly anticipated match-up with Evander Holyfield later that year.

From round one, Douglas was fighting much better than expected; his boxing was crisp, his footwork was smooth, and his defense was looking solid.

Round after round Douglas out-boxed Tyson, and as each round passed it looked more likely that Douglas might just pull off the impossible.

In the closing seconds of round eight Tyson finally landed a big shot—a right uppercut directly on the chin—and Douglas went down.

Controversy lurks around the length of the referee count, but controversy aside, Douglas got up as the referee was milliseconds away from calling 10 and then the round ended.

Douglas battered Tyson in round nine; Tyson later said, “when Douglas got up after I knocked him down and came back at me, I didn’t have it in me.”

Douglas followed up with four clean punches to the head as Tyson fell to the canvas for the first time in his career.

Douglas floors Tyson in the climax of the fight.The referee holds onto Tyson in maybe the most shocking defeat in sports history.

The final moments of the fight saw Tyson on his hands and knees, grabbing for his mouthpiece and barely getting to his feet at the count of 10 when the referee waved the fight off and grabbed ahold of a semi-conscious Tyson.

Prominent sports journalist Dan Rafael summed it up well by writing: “And with that, the mystique of the untouchable, invincible ‘Baddest Man on the Planet’ had been shattered, a moment in time that remains as shocking 25 years later as it was on that quiet Tokyo morning.”

In the post-fight ring interview Douglas was asked how he was able to pull off the win no one thought he could and responded by saying, “Because of my mother…God bless her heart.”